Trifluoroacetic acid → 5-Methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748591Notes

Reaction equation

HRID 1748591 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:24]=[N:25][N:26]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=4)[C:27]=3[CH3:28])=[O:22])=[CH:16][C:15]=2[CH3:39])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH3:28][C:27]1[N:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:38])[F:36])=[CH:31][N:30]=2)[N:25]=[CH:24][C:23]=1[C:21]([NH:20][C:17]1[CH:18]=[N:19][C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:15]([CH3:39])[CH:16]=1)=[O:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86692542N-[6-(1-tert-butyloxycarbonylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Product 1

HCID 866925445-Methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-[6-(1-tert-butyloxycarbonylpiperidin-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (7.0 g) were added dichloromethane (128 ml) and trifluoroacetic acid (26 ml), stirred at room temperature for 2 hours, and then to the reaction solution was added 4 N aqueous solution of sodium hydroxide under ice-cooling. The precipitated solid was washed with n-hexane and water, the obtained solid was dissolved in chloroform, water was added thereto, extracted with chloroform and ethyl acetate, dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The precipitated solid was washed with ethyl acetate to give the titled compound (5.39 g) as a white solid.

Workup

  1. temperaturecooling
  2. washThe precipitated solid was washed with n-hexane and water
  3. dissolutionthe obtained solid was dissolved in chloroform
  4. additionwater was added
  5. extractionextracted with chloroform and ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. washThe precipitated solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-296ad2f0ee5941e49ace802801034000
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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